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Paper | Regular issue | Vol 27, No. 4, 1988, pp.967-972
Published online, 1st January, 1970
DOI: 10.3987/COM-87-4454
New Reractions of 2-Vinylindoles with Azodienophiles: Diels-Alder Reaction versus Michael-type Addition

Ulf Pindur* and Myung-Hwa Kim

*Department of Chemistry and Pharmacy, Institute of Pharmacy, University of Mainz, Saarstrasse 21, D-55122 Mainz, Germany


The reactions of donor- and acceptor-substituted 2-vinylindoles with azodienophiles such as, for example, diethyl azodicarboxylate (DEAD) and 4-phenyl-1,2,4-triazoline-3,5-dione (PTAD) have been examined. Whereas DEAD gives rise to both Diels-Alder and Michael adducts, PTAD reacts preferentially to give novel cycloadducts with pyridazinoindole-type structures.